Halogenated dinaphthyl-dicarboxylic acids



16 wherein the Xs stand for hydrogen atoms Patent ed Aug. 6,1929.

UNITED A-US-TATES.

PATIENT OFFICE.

RICHARD HERZ, OF FRANKFORT-ON-THE-MAIN, AND WERNER ZERWECK, OF FECHEN- REIIMI, NEAR FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNORS T GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORA'JJION OF DELAWARE.

HALOGENATED DINAPHTHYL-DICARBOXYLIG ACIDS.

' No Zilrawing. Original application filed June 23, 1926, Serial No. 118,081, and in Germany July 2, 1925.

I Divided and this application filed May 17, 1928. Serial-No. 278,617.

wherein the Xs stand for, hydrogen atoms, of which one or more may be replaced by a monovalent substituent, are obtained, if the m diazo-compounds of aniinonaphthoic acids of p the general formula:

1 coon OnX r NHI of which one or more may be replacedby a:

monovalent substituent, are treated witha suitable reducing agent, especially with an ammoniacal solution of. cuprous oxide,

90 Accordin to our new process the dinaphthylcarboxy ic acids, their derivatives and nuclear substitution'products can be easily manufactured in a pure statewith an almost theoretical yield.

They are important intermediates for the production of vat dyestuffs.

The following examples will further illus- I trate our newpro'cessj and the products obtained by it. We wish it however to be 80 understood that we are not limited to the I particular conditions nor to the specific products mentioned therein. The parts are by weight.

Ema/m Ze.-248 parts of bromonaphthosty- -ril (see ckstrand Journ. fiir prakt. Chemle, ,vol. 38, page 173) are saponified to the 1-amino-4 bromonaphthalene 8 carboxylic acid, for instance by warming it with caustic soda solution of 10%. This solution is diazotized in the usual manner, and the diazocompound is slowly introduced at an ordinary temperature into an ammoniacal solutlon of cuprous oxide, prepared as described in the parent application. The new 4.1-dibromo-1.1-dinaphthyl-8.8-dicarboxylic acid of'the probable formula:

is obtained as a colorless powder, meltin ab ve ub e in col concentrate sulfuric acid with a red color, which turns to thyl-dicarbox ylic acid corresponding probgreen when warmed. ably to the formula: 25

We claim: Br 1. As new products halogenated dinaph- 5 thyl-dicarboxylic acids corresponding probably to the formula:

Hal

- 'being when dry a colorless powder, melting above 300 (3., soluble in cold concentrated 40 sulfuric acid with a red color, which turns v 81 to green when warmed; being when dry almost colorless powders, In testimony whereof we aflix our sigma-'- soluble in cold concentrated sulfuric acid 'tures.

RICHARD HEBZ.

with a red color.

2. As a new product a brominated dinaph- I l/VERNER ZERWECK. 

